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Outrageous Gossip Girl Guest Stars

Do you remember these guest stars? XOXO, Gossip Girl


RetroEnt here! Your one and only source into the scandalous lives of entertainment’s elite – specifically those of the awesome retro variety. Luckily, we’re right on the money today, because we’re talking about everyone’s favorite subject… Gossip Girl! Yep, unless you’ve been living under a rock for the past few years, you’ll know that Gossip Girl is the bomb diggity. This show follows the lives of those who live on the Upper East Side and basically rule the Big Apple. Serena van der Woodsen steals the show with her trendy take on school uniform (how is she SO perfect?), Blair Waldorf proves that sometimes scheming does work in your favor, Dan Humphrey shows us that it’s okay to be an outsider, Chuck Bass makes us swoon every time he opens his mouth, and the rest of the gang just make us super jealous of their lives. Yuh-huh, their lives are pretty much perfect… except for the fact that Gossip Girl follows their every move and wreaks havoc wherever she goes. Nevertheless, the drama and gossip is what keeps us going during our daily lives, and some of the most outrageous Gossip Girl guest stars just added to that drama. Don’t believe us? Oh, darling. Just check these out. XOXO, Gossip Girl.

Liz Hurley

Outrageous Gossip Girl Guest Stars: Liz Hurley
Okay, so Liz Hurley is a legend. And when she first appeared on Gossip Girl we were all pretty excited. Until she turned up as Diana – and we were pretty confused. We really, really tried to like her, because, you know, Liz Hurley. But Diana was a nasty piece of work, and we just really couldn’t get behind this 40-year-old career woman getting it on with the teen Nate Archibald, and then pretending to be Nate’s best friends mother. We tried, Liz. We really did. It was just all too creepy.

Michael Bloomberg

Outrageous Gossip Girl Guest Stars: Michael Bloomberg
This was such a big deal. In comparison, this was like Lord Alan Sugar turning up on the set of Made in Chelsea. The businessman, politician, author and 10th richest person in the world appeared in the last ever episode (sobs) of Gossip Girl, in the most hilarious fashion. Ever. When Gossip Girl is finally revealed, we see a busy Bloomberg walking the sidewalk to his next meeting, looking at the latest Gossip Girl post – and he couldn’t believe it. ‘I’m shocked – I thought it was Dorota!.’ But let’s be honest, it was never going to be Dorota.

Ivanka Trump

Outrageous Gossip Girl Guest Stars: Ivanka Trump
Yep, you read that right. Ivanka Trump really was on Gossip Girl. And she even took along her husband, Jared Kushner. The pair appeared in the season two episode, ‘Easy J’ at a New York Observer party, and even get toasted by Colin (Serena’s boyfriend at the time). It was kinda cute though, as the episode aired on their one-year wedding anniversary.

Cyndi Lauper

Outrageous Gossip Girl Guest Stars : Cyndi Lauper
There were so many reasons we loved Blair Waldorf. She was beautiful. She was rich. She dated Chuck Bass AND was engaged to a Prince. Oh, and Cyndi Lauper just randomly turned up at her house. Lauper appeared in the second series of the show, and we’ll never forget Dorota’s face when she pinged out of the elevator. She’s just so cool.

Kevin Zegers

Outrageous Gossip Girl Guest Stars: Kevin Zegers
This appearance was a really tough one for us. On the one hand, it’s Kevin Zegers. He’s Canadian. He’s handsome. And we love him. But on the other hand, he was Damien Dalgaard. And we hated Damien Dalgaard. The cute-but-rebellious rich kid Damien was not one of the nice guys on Gossip Girl. Instead, the narcotics dealer turned Spanish tutor was the catalyst for so many of the problems on the Upper East Side.

Krysten Ritter

Outrageous Gossip Girl Guest Stars: Krysten Ritter
Our favorite B in Apartment 23 played Carol Rhodes – teenage style. We all know Lily’s sister as an adult (because she tries to steal a heck load of money) but her younger self was even more rebellious. Krysten Ritter appears in all of the flashback scenes with Carol and Lily and absolutely nails it. And she is just the coolest B around – with the best collection of sunglasses.

Hilary Duff

Outrageous Gossip Girl Guest Stars: Hilary Duff
Nope. Still not over this one. Hilary Duff gave us one of the most bizarre and confusing storylines throughout its 8-year run. Duff appeared on the show as Olivia Burke – the high-flying actress who tries to live a normal life for a while at NYU. She befriends Dan and soon becomes romantically involved with him (because who hasn’t Dan been romantically involved with?). But Vanessa soon got jealous – and then things took an unexpected turn. Soon enough, the three of them spent the evening together. Yeah. We reckon you get the picture.

Vera Wang

Outrageous Gossip Girl Guest Stars: Vera Wang
If you don’t know who Vera Wang is – you would not fit in in the Upper East Side. The famous wedding dress designer likes to make cameo appearances now and then in some of the best American shows, so of course, she had to make an appearance when Blair was wedding dress shopping. You know, when she was about to marry A PRINCE. A REAL LIFE PRINCE. (We still can’t get over it).

Tyra Banks

Outrageous Gossip Girl Guest Stars: Tyra Banks
Who doesn’t love Tyra Banks? The iconic model and America’s Next Top Model host appeared on the show in the episode, ‘Dan de Fleurette’ during season three as Ursula Nyquist. Serena befriends Ursula, a client of KC Cunningham, and soon becomes a huge asset between the company and the actress – to the point where Ursula tells KC Cunningham that she will only stay with the company if Serena continues to work there. Go, Serena.

David O. Russell

Outrageous Gossip Girl Guest Star: David O'Russel
One thing we learned from Gossip Girl was that Serena was the luckiest person in the world. She had no work experience or college degree but somehow managed to work on the hottest film sets of all time. You know, just by chance. During her time working on The Beautiful and the Damned, famous director David O. Russell made a brief cameo, and Serena even got to bring him coffee. Lucky girl.

Lady Gaga

Outrageous Gossip Girl Guest Stars: Lady Gaga
Blair Waldorf gave us incredibly unrealistic expectations of university. If you want to get into the best uni society, all you had to do was buy a round of drinks for everyone, and you’re there. But Blair taught us that to get into the NYU Theater Society; you had to hire Lady Gaga to come and perform for you and your pals. She did do one helluva performance, though.


Outrageous Gossip Girl Guest Stars: Robyn
Gossip Girl just loved to have huge pop stars on their show – because they’re the best, daaahling. Robyn is quite possibly one of the nicest pop stars in existence, but you don’t want to cross her. As Blair found out. Robyn appeared on the show after she was flown in to perform at Blair’s party (we’re lucky if we have streamers and a CD at our parties). In true Robyn form, she gave an amazing performance – but couldn’t leave without publicly shaming the host for her drunken behavior. Ouch.

Tim Gunn

Outrageous Gossip Girl Guest Stars: Tim Gunn
Who doesn’t love Tim Gunn? If you want to make it in fashion – Tim Gunn needs to approve of you. And unfortunately for Little J, he didn’t like her sabotaged collection. And in true Tim Gunn fashion, he sent her out of her office in the best way possible. Nobody wastes Tim Gunn’s time.

Clemence Poesy

Outrageous Gossip Girl Guest Stars: Clemence Poesy
We just couldn’t get enough of this French belle. Our favorite Triwizard Champion and model appeared in multiple episodes and was lucky enough to be one of Chuck Bass’s girlfriends. The infamous lothario met Posey after being shot in France, and soon became part of each other’s lives – but in this case, Chuck’s second life. But unfortunately, it didn’t work out after she saw Chuck for what he really was.

Lisa Loeb

Outrageous Gossip Girl Guest Stars: Lisa Loeb
This singer-songwriter was another one to perform for the cast of Gossip Girl. We first saw Lisa Loeb in series one, when Rufus (we love Rufus) and his band opened up the show for her. But if you remember rightly, she also came back in the finale of the show – as Rufus’ girlfriend!

Brittany Snow

Outrageous Gossip Girl Guest Stars: Brittany Snow
Aww, our favorite Bella. Remember Krysten Ritter as the younger Carol Rhodes. Well, Brittany Snow played Carol’s younger sister, Lily Rhodes. Of course, we all know Lily as being the straight-laced Upper East Side housewife, but Brittany Snow just proved to us that Lily had a bit of an edge to her, too.

Kristen Bell

Outrageous Gossip Girl Guest Stars: Kristen Bell
Okay, so the biggest GG fans will know just how important Kristen Bell is to the show. She’s kind of a big deal. Of course, we all know that she voices the actual Gossip Girl in the opening scenes and throughout the series, but she also makes a personal appearance in the show during the finale – where she and Rachel Bilson tell us who they thought Gossip Girl really was. But Bell knew the real truth….

Tory Burch

Outrageous Gossip Girl Guest Stars: Tory Burch
Because Gossip Girl was such a huge show that focused on relationships, fashion, and luxury, they just had to get the best of the best on the show. And that they did. And the Upper East Side is all about who you know – which is why college dropout Serena was so lucky enough to interview for Tory Burch and her company. You know, as you do.